Bob Dylan wrote this following his split from Suze Rotolo, who he dated between 1961 and 1964. The song details what was the pair's initial courting: "I once loved a girl, her skin it was bronze/With the innocence of a lamb, she was gentle like a fawn/I courted her proudly, but now she is gone/Gone as the season she's taken." Dylan goes on to admit he was a poor partner to Rotolo, who he once cheated on with folk singer, Joan Baez: "Myself, for what I did, I cannot be excused/The changes I was going through can't even be used/For the lies that I told her in hopes not to lose/The could-be dream-lover of my lifetime." Dylan criticizes Rotolo's sister, Carla: "For her parasite sister, I had no respect/Bound by her boredom, her pride to protect/Countless visions of the other she'd reflect/As a crutch for her scenes and her society." Bob and Carla had a very difficult relationship. The song details a violent fight which took place between them in March 1964, on the night Bob and Suze finally split up: "Beneath a bare lightbulb the plaster did pound/Her sister and I in a screaming battleground/And she in between, the victim of sound/Soon shattered as a child 'neath her shadows." Dylan concludes the song reminiscing about Suze: "The wind knocks my window, the room it is wet/The words to say I'm sorry, I haven't found yet/I think of her often and hope whoever she's met/Will be fully aware of how precious she is."

Dylan regrets writing this song. He told Bill Flanagan in 1985: "Oh yeah, that one! I look back and say 'I must have been a real schmuck to write that.' I look back at that particular one and say, of all the songs I've written, maybe I could have left that alone." Dylan added: "I wouldn't really exploit a relationship with somebody. Whereas in 'Ballad in Plain D' I did. Not knowing that I did it. At that time my audience was very small. It overtook my mind so I wrote it. Maybe I shouldn't have used that."

Suze Rotolo forgave Dylan for this seething attack on her sister. Rotolo told Victoria Balfour: "People have asked how I felt about those songs that were bitter, like 'Ballad in Plain D,' since I inspired some of those too; yet I never felt hurt by them. I understood what he was doing. It was the end of something and we both were hurt and bitter. His art was his outlet, his exorcism. It was healthy. That was the way he wrote out his life, the loving songs, the cynical songs, the political songs, they are all part of the way he saw his world and lived his life, period."

Another Side of Bob Dylan was Dylan's fourth album. Dylan deviated from politically-charged lyrics to instead write on more personal issues for this album - a move which prompted backlash from fans who claimed he had lost touch with his audience.